#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/33/2223369.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2223369
loop_
_publ_author_name
'Monroe, Thomas Blake'
'Moazami, Yasamin'
'Jones, Daniel S.'
'Ogle, Craig A.'
_publ_section_title
;
 Methyl 5,6-dimethoxy-1H-indole-2-carboxylate
;
_journal_coeditor_code           FJ2241
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2353
_journal_paper_doi               10.1107/S1600536809034667
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C12 H13 N1 O4'
_chemical_formula_moiety         'C12 H13 N1 O4'
_chemical_formula_sum            'C12 H13 N O4'
_chemical_formula_weight         235.23
_chemical_name_systematic
;
Methyl 5,6-dimethoxy-1H-indole-2-carboxylate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.0768(19)
_cell_length_b                   7.7232(11)
_cell_length_c                   17.678(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      43.03
_cell_measurement_theta_min      10.03
_cell_volume                     2331.5(5)
_computing_cell_refinement       'CAD-4 EXPRESS  (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS  (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
;ORTEP-3 for Windows (Farrugia, 1997) and Mercury
(Macrae et al.,  2006)
;
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       'Non-profiled ω/2θ'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9909
_diffrn_reflns_theta_full        67.41
_diffrn_reflns_theta_max         67.41
_diffrn_reflns_theta_min         5
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 171
_diffrn_standards_interval_time  57
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.85
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.34
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.117
_refine_ls_extinction_coef       0.0047(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2098
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0613P)²+0.2248P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1015
_reflns_number_gt                1522
_reflns_number_total             2098
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fj2241.cif
_cod_data_source_block           I
_cod_database_code               2223369
_cod_database_fobs_code          2223369
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N 0.05760(8) 0.76815(19) 0.51504(7) 0.0509(3) Uani d . 1 . .
O O1 0.07015(8) 1.05091(17) 0.41553(7) 0.0727(4) Uani d . 1 . .
O O2 0.17099(7) 0.92154(18) 0.35786(7) 0.0722(4) Uani d . 1 . .
O O3 0.00702(6) 0.30330(14) 0.69682(6) 0.0564(3) Uani d . 1 . .
O O4 0.12332(7) 0.14080(15) 0.64271(7) 0.0656(4) Uani d . 1 . .
C C2 0.11320(9) 0.7786(2) 0.45863(8) 0.0516(4) Uani d . 1 . .
C C3 0.15832(9) 0.6316(2) 0.46040(8) 0.0530(4) Uani d . 1 . .
H H3 0.2001 0.6062 0.4285 0.064 Uiso calc R 1 . .
C C4 0.15041(8) 0.3618(2) 0.54858(8) 0.0495(4) Uani d . 1 . .
H H4 0.1918 0.2997 0.5277 0.059 Uiso calc R 1 . .
C C5 0.10882(9) 0.2958(2) 0.60783(8) 0.0476(4) Uani d . 1 . .
C C6 0.04402(8) 0.3882(2) 0.63953(8) 0.0453(4) Uani d . 1 . .
C C7 0.02331(8) 0.5479(2) 0.61286(8) 0.0459(4) Uani d . 1 . .
H H7 -0.018 0.6096 0.634 0.055 Uiso calc R 1 . .
C C8 0.06679(8) 0.6150(2) 0.55251(8) 0.0448(4) Uani d . 1 . .
C C9 0.12971(8) 0.5256(2) 0.51953(8) 0.0466(4) Uani d . 1 . .
C C10 0.11447(10) 0.9300(2) 0.41017(9) 0.0556(4) Uani d . 1 . .
C C11 0.17434(13) 1.0657(4) 0.30566(12) 0.0936(8) Uani d . 1 . .
H H11A 0.1271 1.0693 0.2763 0.14 Uiso calc R 1 . .
H H11B 0.2184 1.0517 0.2725 0.14 Uiso calc R 1 . .
H H11C 0.1797 1.1718 0.3335 0.14 Uiso calc R 1 . .
C C12 0.18869(10) 0.0457(2) 0.61719(11) 0.0661(5) Uani d . 1 . .
H H12A 0.1826 0.0201 0.5644 0.099 Uiso calc R 1 . .
H H12B 0.1925 -0.0604 0.6452 0.099 Uiso calc R 1 . .
H H12C 0.2354 0.1128 0.6246 0.099 Uiso calc R 1 . .
C C13 -0.05334(10) 0.3942(2) 0.73565(10) 0.0622(5) Uani d . 1 . .
H H13A -0.0324 0.4989 0.7568 0.093 Uiso calc R 1 . .
H H13B -0.0737 0.3228 0.7755 0.093 Uiso calc R 1 . .
H H13C -0.0946 0.4221 0.7009 0.093 Uiso calc R 1 . .
H H1 0.0202(10) 0.852(2) 0.5251(10) 0.064(5) Uiso d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 0 4
0 -2 1
0 2 1
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 N C2 . . 108.82(14) ?
C8 N H1 . . 126.2(11) ?
C2 N H1 . . 125.0(11) ?
C10 O2 C11 . . 115.57(16) ?
C6 O3 C13 . . 117.19(12) ?
C5 O4 C12 . . 117.03(13) ?
C3 C2 N . . 108.74(14) ?
C3 C2 C10 . . 132.24(14) ?
N C2 C10 . . 119.01(15) ?
C2 C3 C9 . . 107.56(14) ?
C2 C3 H3 . . 126.2 ?
C9 C3 H3 . . 126.2 ?
C5 C4 C9 . . 118.94(14) ?
C5 C4 H4 . . 120.5 ?
C9 C4 H4 . . 120.5 ?
C4 C5 O4 . . 125.31(14) ?
C4 C5 C6 . . 121.15(15) ?
O4 C5 C6 . . 113.54(13) ?
O3 C6 C7 . . 124.82(13) ?
O3 C6 C5 . . 114.20(13) ?
C7 C6 C5 . . 120.98(14) ?
C6 C7 C8 . . 117.36(13) ?
C6 C7 H7 . . 121.3 ?
C8 C7 H7 . . 121.3 ?
N C8 C7 . . 129.03(14) ?
N C8 C9 . . 108.22(13) ?
C7 C8 C9 . . 122.74(14) ?
C8 C9 C4 . . 118.80(14) ?
C8 C9 C3 . . 106.66(14) ?
C4 C9 C3 . . 134.55(14) ?
O1 C10 O2 . . 123.01(16) ?
O1 C10 C2 . . 124.67(15) ?
O2 C10 C2 . . 112.32(16) ?
O2 C11 H11A . . 109.5 ?
O2 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
O2 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
O4 C12 H12A . . 109.5 ?
O4 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
O4 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
O3 C13 H13A . . 109.5 ?
O3 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
O3 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N C8 . 1.365(2) ?
N C2 . 1.3792(19) ?
N H1 . 0.926(19) ?
O1 C10 . 1.206(2) ?
O2 C10 . 1.338(2) ?
O2 C11 . 1.447(2) ?
O3 C6 . 1.3619(18) ?
O3 C13 . 1.4235(19) ?
O4 C5 . 1.3695(19) ?
O4 C12 . 1.410(2) ?
C2 C3 . 1.373(2) ?
C2 C10 . 1.449(2) ?
C3 C9 . 1.415(2) ?
C3 H3 . 0.93 ?
C4 C5 . 1.364(2) ?
C4 C9 . 1.410(2) ?
C4 H4 . 0.93 ?
C5 C6 . 1.431(2) ?
C6 C7 . 1.367(2) ?
C7 C8 . 1.399(2) ?
C7 H7 . 0.93 ?
C8 C9 . 1.404(2) ?
C11 H11A . 0.96 ?
C11 H11B . 0.96 ?
C11 H11C . 0.96 ?
C12 H12A . 0.96 ?
C12 H12B . 0.96 ?
C12 H12C . 0.96 ?
C13 H13A . 0.96 ?
C13 H13B . 0.96 ?
C13 H13C . 0.96 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N H1 O1 5_576 0.926(19) 2.011(19) 2.867(2) 152.9(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3964405
